A woman I'm interested in has shown signs of mutual interest. She's a single mom who in unattached. Last week while chatting she told me when she's not hanging with her daughter she volunteers at two separate organizations. She commented that she wants to cut back on her volunteer hours "to have more time to herself.". She offered this information without me asking about her free time or what she does on weekends.

Does this sound like a subtle invitation for me to ask her out or get her number?

As with many guys, I often have trouble reading signs that a woman wants me to make a move.

As someone who entered the dating pool first at 18, then again at 36 (divorce), and the last time at 39 (after a 3 year relationship went bust), I can tell you that the woman's (and your) age is a determining factor. The older a person is, IMO, the more direct you can be. I'm not saying you can ask her "Hey, wanna shag?" but I also know that as I got older, the less women cared about the "opening gambit" and it was more about the middle and end game. While a "coffee" date is cliche, no matter how old a woman is, she wants to feel safe, so the first date needs to be something non-threatening and friendly, e.g. a walk, coffee, or maybe a daytime movie. OTOH, you can just come right out and ask "Would you like to go out sometime?" That way, you will know her intentions right away - if she says "no" then you are either misreading her or she is not yet ready to make her intentions clear. If she says "yes" well, you're all set. If you want to make it safer, you can ask her to coffee, a walk, or something that people do even if they are not "dating." Dinner or lunch is fine, provided it is not a restaurant that screams "Romance!" Maybe something like "I have read about a new Asian/French/etc. restaurant and want to try it...would you like to join me?" DON'T OFFER TO PAY for goodness sake. For myself, I always took the most direct approach as I got older, simply because I didn't want to beat around the bush (hoo boy...I know). Some women liked that, some didn't.

Lastly, I agree with Sun Dummy...I have lots of regrets...not for things I have done, but things left unsaid and undone. I've told some women things that I, in hindsight, probably should've kept to myself (unrequited love and all that), but at least I won't be left wondering "If only...."

Bill, excellent take on this and I planned to do it this way (the casual friend-like activity first, then go from there), so nice to read someone who agrees with my thoughts exactly. I've found the "wanna go out sometime" approach often doesn't work too well as its too direct and scares some women off, but as you said it may work with older women.

I think you are right being a bit cautious seeing that she is a co-worker, a misunderstanding can lead to interoffice trouble. Lunch or coffee is a pretty safe way to co-mingle with a co-worker.

It it doesn't work out and you are still interested in finding someone I would suggest internet dating. I have recently try it and have had pretty good success with it so far. As Bill says, as we get older the posturing gets less important, the end result more so. I find most women here in LA around my age want someone who is serious about having a relationship, it seems they are finding a lot of men are not that serious. So showing that you are serious puts you ahead in the game. Also as Bill pointed out, women want to feel safe, so take it slowly and show that you are a safe staple guy that they can count on.

Update: the object of my affection gave off too many red flags to even consider pursuing... the main one being ditzy, unreliable, forgetful, and flaky. This woman could not remember when Easter was, two days after Easter Sunday (andwe had talked about our individual plans the Friday before Easter)!!! Put several other recent examples like this together and I start thinking, "Do I want to date someone this wigged out mentally?". Disappointingly, the answer was no. She is also a divorced single mother, which oftentimes can be a recipe for disaster in the long run (especially when the child is only 10 years old).

One good thing about potential dating of coworkers is that you can screen out the red flags before even going on one date!

I understand about steering clear of red flags, but after the age of 30 or so, the great majority of unmarried women you'll meet will fall into the category of "divorced single mother" so I'm not sure that's a red flag in itself.

Of course, if she's "wigged out mentally" as you say, that's a pretty big red flag right there!

I understand about steering clear of red flags, but after the age of 30 or so, the great majority of unmarried women you'll meet will fall into the category of "divorced single mother" so I'm not sure that's a red flag in itself.

I have to agree, and when we get to women in their 40s its almost a red flag if they are not divorced single mothers.

So despite the conclusion reached above, I've found it hard to crush my crush on this woman. We had a lunch planned, wherein I had to adjust my schedule. She called the day before saying she "forgot" she had to pick up her daughter from school at lunchtime and asked if we could reschedule to the next week. I finally suggested we just drop the idea because it didn't seem she was into the idea with all this forgetting and excuses. She then said we can go downtown and grab lunch sometime...? Why would you even mention the idea if you obviously had no intention of following through??? I noticed all the cancellations were always suggested being rescheduled to the next week instead of that same week, and no exact day was ever offered. Also saying sometime is about as vague and noncommittal as you can get. I have gotten it through my head this ain't gonna happen, yet it's still hard because I see her every day. What's worse, unrequited love in the workplace or an office romance gone sour? I have experienced the latter but not never the former...

sorry to hear how this is (not) going for you - I'd suggest unrequited love is better than the office romance gone sour though, usually less of the unpleasant fall out.

I suspect backing off and seeing if she comes to you to make a date might be the way to go. Then if she cancels again you are in the place to say Ok enough is enough and ask her to explain what is going on to you.

If she does not come to you then either she is not interested enough or there is some much more complex set of circumstances (such as she turns into a werewolf at night, her ex is jealously aggresive or she has a serious illness etc etc) - both of which might be reasons to step away......

As for the unrequited crush, I know that one - i was in love with a girl at school for three years but too painfully shy to say or do anything other than blush look stupid (at least that's how I felt I looked).....I don't have any suggestions for that one that does not sound trite when typed, so just wishing you the best of luck all round.

Just agree with her, maybe in the future whenever that is you two can get lunch, but for now just move on. Either she's not that interested as you suspect, or she's too busy right now, or she's a mess and can't get her act together for a simple lunch. In any case it's not happening right now, maybe that will change but who knows. Forcing the issue won't do anything and dwelling on it is not good for you.

So finally she brought up lunch and it was to be two weeks later. I suggested we meet up for drinks instead a couple days later. She seemed enthusiastic enough about this and gave me her number. When I texted her to see what our schedules were like to set it up, she replied: "I'll have to see about drinks. It's unlikely I don't have my daughter most evenings.".

Whenever a girl says "we'll see" or "maybe" it means NO. So she had already flaked on two lunches and was now backpedaling on the drinks idea. Does this sound like game playing to you, or a woman getting off on male attention while having no intention of getting involved? Or both? It seems like she enjoys this shit and won't stop until I walk away for good...